Ethyl orthoformate → 7-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 371919Notes

Reaction equation

HRID 371919 reaction equation
[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]([CH3:11])=[N:6][C:7]=1[NH:8][CH2:9][CH3:10].[CH2:18](OC(OCC)OCC)C>>[Cl:17][C:3]1[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]([CH3:11])[N:6]=[C:7]2[N:8]([CH2:9][CH3:10])[CH:18]=[N:1][C:2]=12

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 123876185-Amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester

Product 1

HCID 123876387-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Procedure

25.7 g. of 5-amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester (0.1 mol.) is refluxed for 12 hours with 100 ml. of orthoformic acid triethyl ester with stirring. The excess ester is removed in vacuo and the oily residue distilled to obtain 7-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, b.p. 195°/0.01. Yield 23 g. (86%).

Workup

  1. customThe excess ester is removed in vacuo
  2. distillationthe oily residue distilled

Sources & evidence

ORD record
ord-dcc55302b9f845fc86fd133e3e051aec
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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